N-[1-D,L-(benzyloxycarbonyl)tridecyl]-1,2,3,4-tetra-O-acetyl-β-D-glucopyranuronamide

Base Information

Chemical Name:N-[1-D,L-(benzyloxycarbonyl)tridecyl]-1,2,3,4-tetra-O-acetyl-β-D-glucopyranuronamide
CAS No.:669011-11-4
Molecular Formula:C₃₅H₅₁NO₁₂
Molecular Weight:677.789
Hs Code.:

Synonyms:N-[1-D,L-(benzyloxycarbonyl)tridecyl]-1,2,3,4-tetra-O-acetyl-β-D-glucopyranuronamide

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Chemical Property of N-[1-D,L-(benzyloxycarbonyl)tridecyl]-1,2,3,4-tetra-O-acetyl-β-D-glucopyranuronamide

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Technology Process of N-[1-D,L-(benzyloxycarbonyl)tridecyl]-1,2,3,4-tetra-O-acetyl-β-D-glucopyranuronamide

There total 3 articles about N-[1-D,L-(benzyloxycarbonyl)tridecyl]-1,2,3,4-tetra-O-acetyl-β-D-glucopyranuronamide which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 75.0%

: 1-D,L-(benzyloxycarbonyl)tridecylammonium trifluoroacetate

: 62133-77-1,67919-37-3,83023-73-8,85165-61-3,95722-13-7,98301-58-7,103730-05-8,104195-04-2
1,2,3,4-tetra-O-acetyl-β-D-glucopyranuronic acid

: 669011-11-4
N-[1-D,L-(benzyloxycarbonyl)tridecyl]-1,2,3,4-tetra-O-acetyl-β-D-glucopyranuronamide

Guidance literature:: 1,2,3,4-tetra-O-acetyl-β-D-glucopyranuronic acid; With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; at 20 ℃; for 0.166667h;

1-D,L-(benzyloxycarbonyl)tridecylammonium trifluoroacetate; In tetrahydrofuran; for 18h;
DOI:10.1021/jm030474j

Reference yield:

: 6556-12-3,489-91-8,528-16-5,552-12-5,577-46-8,643-33-4,2240-07-5,6294-16-2,10133-02-5,18402-78-3,18968-14-4,21179-08-8,23018-83-9,33599-45-0,33599-46-1,46171-67-9,46171-69-1,46172-26-3,70021-34-0,71031-08-8,104195-06-4,106499-29-0,124817-72-7
D-glucuronic acid

: 669011-11-4
N-[1-D,L-(benzyloxycarbonyl)tridecyl]-1,2,3,4-tetra-O-acetyl-β-D-glucopyranuronamide

Guidance literature:: Multi-step reaction with 2 steps

1.1: I₂ / 3 h / 0 - 25 °C

1.2: 55 percent / MeOH / 18 h / 25 °C

2.1: DIEA; HBTU / tetrahydrofuran / 0.17 h / 20 °C

2.2: 75 percent / tetrahydrofuran / 18 h

With iodine; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran;
DOI:10.1021/jm030474j

Reference yield:

: 474426-72-7
acetic 1,2,3,4-tetra-O-acetyl-β-D-glucopyranuronic anhydride

: 669011-11-4
N-[1-D,L-(benzyloxycarbonyl)tridecyl]-1,2,3,4-tetra-O-acetyl-β-D-glucopyranuronamide

Guidance literature:: Multi-step reaction with 2 steps

1.1: 100 percent / H₂O / tetrahydrofuran / 18 h

2.1: DIEA; HBTU / tetrahydrofuran / 0.17 h / 20 °C

2.2: 75 percent / tetrahydrofuran / 18 h

With water; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran;
DOI:10.1021/jm030474j